Products for the treatment of the iron chlorosis
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example 1
2-(2-((2-hydroxybenzyl)amino)ethylamino)-2-(2-hydroxyphenyl)acetic acid
Step 1. Intermediate of formula (II) (X1=2-hydroxyphenyl, Y═(CH2)2, X2=2-hydroxybenzyl)
[0062]To a solution of the 2-(2-aminoethylamino)-2-(2-hydroxyphenyl)acetic acid hydrochloride in water at pH 7.3, was added an equimolar amount of salicylaldehyde in ethanol. After stirring for 1 h at room temperature, the title Schiff base was filtered and obtained as a solid in 80% yield.
[0063]1H-NMR (300 MHz, DMSO-d6, 2.5, ppm): δ=8.54 (s, 1H, CH═N), 7.48 (d, 1H, J=7.5 Hz, Ar), 7.34 (t, 1H, J=7.62 Hz, Ar), 7.30 (d, 1H, J=7.32 Hz, Ar), 7.18 (m, 1H, Ar), 6.92-6.70 (m, 4H, Ar), 4.62 (s, 1H, CH), 3.83 (m, 4H, CH2), 3.15 (m, 1H, CH2), 3.02 (m, 1H, CH2).
Step 2. 2-(2-((2-hydroxybenzyl)amino)ethylamino)-2-(2-hydroxyphenyl)acetic acid
[0064]The hydrogenation of the of the Schiff base obtained in Step 1 in MeOH (10% Pd / C) at room temperature yielded the title product as brown solid (80%).
[0065]1H-NMR (500 MHz, D2O, 4.8(HDO), ppm): δ=7...
example 2
2-(2-((2-hydroxy-1-naphtyl)methylamino)ethylamino)-2-(2-hydroxyphenyl)acetic acid
Step 1. Intermediate of formula (II) (X1=2-hydroxyphenyl, Y═(CH2)2, X2=2-hydroxy-1-naphtyl)
[0066]Following Example 1, but starting from equimolar amounts of 2-(2-aminoethylamino)-2-(2-hydroxyphenyl)acetic acid hydrochloride and 1-formyl-β-naphtol the the Schiff base of the title was obtained as yellow solid in 70% yield.
[0067]1H-NMR (300 MHZ,DMSO, 2.5, ppm): δ=9.11 (s, 1H, CH—N), 8.055 (d, 1H, J=8.35 Hz, Ar), 7.72 (d, 1H, J=9.44 Hz, Ar), 7.63 (d, 1H, J=7.10 Hz, Ar), 7.42 (d, 2H, J=7.07 Hz, Ar), 7.25 (d, 1H, J=9.44 Hz, Ar), 7.17 (d, 2H, J=7.11 Hz, Ar), 6.75-6.67 (m, 2H, Ar), 4.43 (s, 1H), 3.86-3.78 (m, 2H, CH2), 3.2-3.02 (m, 1H CH2), 2.92-2.8 (m, 1H, CH2).
Step 2. 2-(2-((2-hydroxy-1-naphtyl)methylamino)ethylamino)-2-(2-hydroxyphenyl)acetic acid
[0068]A mixture of equimolar amounts of the Schiff base obtained in Step 1, NaBH3CN and a catalytic amount of Zn2Cl in MeOH was stirred at room temperature for 3 ...
example 3
2-(2-((pyridin-2-yl)methylamino)ethylamino)-2-(2-hydroxyphenyl)acetic acid
Step 1. Intermediate of formula (II) (X1=2-hydroxyphenyl, Y═(CH2)2, X2=pyridin-2-yl)
[0070]The procedure of Example 1 is followed, but starting from equimolar amounts of 2-(2-aminoethylamino)-2-(2-hydroxyphenyl)acetic acid hydrochloride and 2-pyridinecarboxaldehyde at pH 7. After 20 h at room temperature the solvent was removed and the title Schiff base was obtained as yellow solid in 90% yield.
[0071]1H-NMR (300 MHZ,DMSO, 2.5, ppm): δ=8.63 (bs, 1H, J=4.77 Hz, CH═N), 8.5-8.1 (m, 1H, Ar), 8.0-7.84 (m, 2H, Ar), 7.46 (t, 1H, Ar J=6.58 Hz,), 7.21-7.1 (m, 1H, Ar ), 7.05-6.95 (m, 1H, Ar ), 6.88-6.73 (m, 2H, Ar), 4.59 (s, 1H, CH), 3.9 (m, 2H, CH2), 3.1-3.0 (m, 2H, CH2).
Step 2. 2-(2-((pyridin-2-yl)methylamino)ethylamino)-2-(2-hydroxyphenyl)acetic acid
[0072]A mixture of equimolar amounts of the Schiff base obtained in Step 1 and NaBH4 in MeOH was stirred at room temperature for 20 h. The solvent was removed by evaporati...
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